Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
  • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
  • A61K8/731—Cellulose; Quaternized cellulose derivatives
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/04—Preparations for permanent waving or straightening the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95

Definitions

• the present invention relates to a cosmetic composition, especially a hair composition, based on particular dicarbonyl compounds, and also to a process for straightening keratin fibers such as the hair, using this composition.
• compositions which make it possible to introduce a temporary change to their head of hair, while targeting good persistence of the effect produced.
• One of the treatments known for modifying the texture of the hair consists in combining heat and a composition comprising formol. This treatment is especially effective for imparting a better appearance to damaged hair and/or for treating long hair and curly hair.
• the action of formol is associated with its ability to crosslink proteins by reaction on the nucleophilic sites thereof.
• the heat used may be that of an iron (flat tongs or crimping iron), the temperature of which may generally be up to 200° C. or more.
• iron flat tongs or crimping iron
• Patent application WO 2011/104 282 thus proposed a novel process for semi-permanently straightening the hair, which consists in applying an ⁇ -keto acid solution to the hair for 15 to 120 minutes, then drying and, finally, straightening the head of hair with an iron at a temperature of about 200° C.
• the ⁇ -keto acid employed is preferably glyoxylic acid.
• glyoxylic acid can give rise to significant limitations; in particular, when the scalp is sensitive and/or irritated. Its volatility, amplified by the use of heat (iron), can also be a problem.
• the aim of the invention is to develop a straightening/relaxing composition which is stable over time and which makes it possible to straighten/relax and/or reduce the volume of keratin fibers in an efficient and persistent manner while limiting damage to the hair, while at the same time retaining comfort at the time of application for the user of the composition, but also for the hairdresser who applies it.
• composition comprising
• a subject of the invention is also a process for straightening keratin fibers, in particular the hair, which comprises the application to said fibers of the composition of the invention, followed by a straightening step using a straightening iron at a temperature of at least 150° C., preferably between 150 and 250° C.
• the composition of the invention is stable.
• the composition of the invention, and the process for treating keratin fibers using the compounds of formula (I), the cellulose-based polymers and amphoteric surfactants as defined previously allow good straightening of keratin fibers while limiting the degradation of these keratin fibers, even when the application of the composition(s) is followed by a heat treatment, especially by means of a hair-straightening iron, and have an appreciated working quality, especially without excessive vaporization of the composition at the time of straightening.
• the composition and the process for treating keratin fibers according to the invention also make it possible to limit the change in the color of the fibers and also the problems of breakage of said fibers such as the hair.
• the composition and the process of the invention will also improve the physical properties of the hair, by durably reducing the frizziness effect of the hair.
• composition according to the invention does not comprise any coloring agent or any reducing agent.
• the term “coloring agents” means agents for coloring keratin fibers, such as direct dyes, pigments or oxidation dye precursors (bases and couplers). If they are present, their content does not exceed 0.001% by weight relative to the total weight of the composition. Specifically, at such a content, only the composition would be dyed, i.e. no dyeing effect would be observed on the keratin fibers.
• oxidation dye precursors, oxidation bases and couplers are colorless or sparingly colored compounds, which, via a condensation reaction in the presence of an oxidizing agent, give a colored species.
• direct dyes these compounds are colored and have a certain affinity for keratin fibers.
• reducing agent means an agent that is capable of reducing the disulfide bonds of the hair, such as compounds chosen from thiols, alkaline sulfites, hydrides and phosphines.
• the dicarbonyl compounds of formula (I) or derivatives thereof may be in free form, but also in their hydrate forms or in the form of their salts, preferably in free form or in the form of hydrates.
• esters and amides may be synthesized via conventional esterification or amidation processes, from the corresponding acids well known to those skilled in the art.
• esters are obtained, for example, from the acids of formula (I) and from a mono- or polyalcohol.
• mono- or polyalcohol means an organic compound comprising one hydroxyl group (monoalcohol) or at least two hydroxyl groups (polyalcohol or polyol); said hydroxylated organic compound possibly being aliphatic, acyclic, linear or branched, or (hetero)cyclic, such as sugars (monosaccharides or polysaccharides) or sugar alcohols.
• the polyalcohol comprises from 2 to 100 hydroxyl groups, preferentially from 2 to 20 hydroxyl groups, even more preferentially from 2 to 10 hydroxyl groups, and better still 2 or 3 hydroxyl groups.
• the mono- or polyalcohol is chosen from methanol, ethanol, propanol, isopropanol, butanol, hexanol, ethylene glycol, glycerol, dihydroxyacetone, glucose, sorbitol and menthol.
• the amides are obtained, for example, from the acid of formula (I) and from an organic mono- or polyamine.
• mono- or polyamine means an organic compound comprising one amino group (monoamine) or at least two (and preferably from 2 to 100, better still from 2 to 20) amino groups; said organic compound possibly being aliphatic, acyclic, linear or branched or (hetero)cyclic.
• amino group means a primary amine group —NH 2 , or a secondary amino group >NH.
• the mono- or polyamine is preferably aliphatic.
• This amine is preferably chosen from methylamine, ethylamine, propylamine, isopropylamine, butylamine, hexylamine, monoethanolamine, monopropanolamine, propane-1,2,3-triamine and diaminoacetone.
• the acetals and hemiacetals of the acids of formula (I) may be obtained, for example, from the reaction of alcohols with blocked forms of the acids, followed by hydrolysis.
• the alcohols may be the same as those mentioned for the esters.
• the acetals may also be cyclic acetals.
• the salts may be salts derived from the interaction of the compounds of formula (I) with acids or bases, it being possible for the acids or bases to be of organic or mineral nature.
• the salts are salts derived from the interaction of the compounds of formula (I) with bases.
• Alkali metal or alkaline-earth metal salts, and in particular the sodium salts, will in particular be mentioned.
• dicarbonyl compounds of formula (I) will be referred to as “dicarbonyl compounds and/or derivatives thereof”.
• the dicarbonyl compound(s) are of formula (I) with R representing i) a hydrogen atom or ii) a linear or branched C 1 -C 6 alkyl group optionally substituted with a carboxyl group.
• the compounds of formula (I) are chosen from glyoxylic acid, pyruvic acid, a derivative thereof, a salt thereof and a hydrate thereof.
• the dicarbonyl compound(s) of formula (I) of the invention are chosen from glyoxylic acid and derivatives thereof: glyoxylic acid and its hydrate form (HO) 2 CH—C(O)—OH, for example, the glyoxylic acid as an aqueous 50% solution sold by the company Merck.
• glyoxylic acid derivatives mention may be made of glyoxylic acid esters, glyoxylic acid amides, glyoxylic acid (thio)acetals and hemi(thio)acetals, glyoxylic acid ester (thio)acetals and hemi(thio)acetals.
• the glyoxylic acid esters are obtained, for example, from glyoxylic acid and a mono- or polyalcohol, especially those mentioned previously.
• the mono- or polyalcohol is chosen from methanol, ethanol, propanol, isopropanol, butanol, hexanol, ethylene glycol, glycerol, dihydroxyacetone, glucose, sorbitol and menthol.
• esters By way of esters, mention may in particular be made of methyl glyoxylate, ethyl glyoxylate, glyceryl glyoxylate, dihydroxyacetone glyoxylate, glyceryl diglyoxylate or triglyoxylate, sorbitol mono-, di- or triglyoxylate, glucose mono-, di- or triglyoxylate, menthyl glyoxylate, and acetals, hemiacetals and hydrates thereof.
• the glyoxylic acid amides are, for example, obtained from glyoxylic acid and an organic mono- or polyamine, especially those described previously.
• This amine is preferably chosen from methylamine, ethylamine, propylamine, isopropylamine, butylamine, hexylamine, monoethanolamine, monopropanolamine, propane-1,2,3-triamine and diaminoacetone.
• the glyoxylic acid (thio)acetals and hemi(thio)acetals may be obtained, for example, from the reaction of alcohols, for the acetals or hemiacetals, or of thiols, for the thioacetals or hemithioacetals, with blocked forms of glyoxylic acid, followed by hydrolysis.
• the alcohols may be the same as those mentioned for the esters.
• the thiols may be equivalents (referred to as mono- or polythiols) to the mono- or polyalcohols mentioned above, except for the fact that the hydroxyl function(s) of said mono- or polyalcohols are replaced with one or more thiol functions SH of the mono- or polythiols.
• the acetals or thioacetals may also be cyclic (thio)acetals.
• the compound of formula (I) is glyoxylic acid in hydrate form.
• compositions according to the invention may be in any of the formulation forms conventionally used, and in particular in the form of an aqueous, alcoholic or aqueous-alcoholic, or oily solution or suspension; a solution or a dispersion of the lotion or serum type; an emulsion, in particular of liquid or semi-liquid consistency, of the O/W, W/O or multiple type; a suspension or emulsion of soft consistency of cream (O/W) or (W/O) type; an aqueous or anhydrous gel, or any other cosmetic form.
• compositions may be packaged in pump-action bottles or in aerosol containers, so as to apply the composition in vaporized (lacquer) form or in the form of a mousse.
• Such packaging forms are indicated, for example, when it is desired to obtain a spray or a mousse, for treating the hair.
• the composition preferably comprises at least one propellant.
• compositions of the invention may be aqueous or anhydrous. They are preferably aqueous and then comprise water at a concentration ranging from 5% to 98%, better still from 5% to 50% and even better still from 10% to 40% by weight relative to the total weight of the composition.
• the composition of the invention is in the form of an aqueous composition comprising from 0.1% to 20% of dicarbonyl compounds of formula (I) and/or derivatives thereof, preferably at least 3% of dicarbonyl compounds of formula (I) and/or derivatives thereof, preferentially from 3% to 10% by weight relative to the total weight of the composition.
• the composition comprises at least one cellulose-based polymer.
• the cellulose-based polymers may be anionic, cationic, amphoteric or nonionic polymers.
• the term “cellulose-based” polymer means any polysaccharide compound having in its structure sequences of glucose residues linked together via ⁇ -1,4 bonds; in addition to unsubstituted celluloses, the cellulose derivatives may be anionic, cationic, amphoteric or nonionic.
• the cellulose-based polymers of the invention may be chosen from unsubstituted celluloses, including those in a microcrystalline form, and cellulose ethers. Among these cellulose-based polymers, cellulose ethers, cellulose esters and cellulose ester ethers are distinguished.
• cellulose esters are mineral esters of cellulose (cellulose nitrates, sulfates, phosphates, etc.), organic cellulose esters (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates and acetatetrimellitates, etc.), and mixed organic/mineral esters of cellulose, such as cellulose acetatebutyrate sulfates and cellulose acetatepropionate sulfates.
• cellulose ester ethers mention may be made of hydroxypropylmethylcellulose phthalates and ethylcellulose sulfates.
• the cellulose-based polymer(s) are nonionic.
• (C 1 -C 4 )alkylcelluloses such as methylcelluloses and ethylcelluloses (for example, Ethocel standard 100 Premium from Dow Chemical);
• (poly)hydroxy(C 1 -C 4 )alkylcelluloses such as hydroxymethylcelluloses, hydroxyethylcelluloses (for example, Natrosol 250 HHR provided by Aqualon) and hydroxypropylcelluloses (for example, Klucel EF from Aqualon); mixed (poly)hydroxy(C 1 -C 4 )alkyl(C 1 -C 4 )alkylcelluloses, such as hydroxypropylmethylcelluloses (for example, Methocel E4M from Dow Chemical), hydroxyethylmethylcelluloses, hydroxyethylethylcelluloses (for example, Bermocoll E 481 FQ from Akzo Nobel) and hydroxybutyl
• the cellulose-based polymer(s) are anionic.
• anionic cellulose ethers mention may be made of (poly)carboxy(C 1 -C 4 )alkylcelluloses and salts thereof. Examples that may be mentioned include carboxymethylcelluloses, carboxymethylmethylcelluloses (for example Blanose 7M from the company Aqualon) and carboxymethylhydroxyethylcelluloses, and the sodium salts thereof.
• the cellulose-based polymer(s) are cationic.
• cationic cellulose ethers mention may be made of cationic cellulose derivatives such as cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer, and described in particular in U.S. Pat. No. 4,131,576, such as (poly)hydroxy(C 1 -C 4 )alkyl celluloses, for instance hydroxymethyl-, hydroxyethyl- or hydroxypropylcelluloses grafted especially with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
• the commercial products corresponding to this definition are more particularly the products sold under the names Celquat® L 200 and Celquat® H 100 by the company National Starch.
• the cellulose-based polymers of the invention are nonionic cellulose-based polymers comprising alkyl chains comprising from 1 to 6 carbon atoms.
• the cellulose-based polymer(s) of the invention are chosen from cellulose ethers, in particular hydroxyalkylalkylcelluloses, such as (poly)hydroxy(C 1 -C 4 )alkyl (C 1 -C 4 )alkylcelluloses, in particular hydroxypropylmethylcelluloses (for example, Methocel F4M from Dow Chemical), hydroxyethylmethylcelluloses, hydroxyethylethylcelluloses (for example, Bermocoll E 481 FQ from Akzo Nobel) and hydroxybutylmethylcelluloses.
• cellulose ethers in particular hydroxyalkylalkylcelluloses, such as (poly)hydroxy(C 1 -C 4 )alkyl (C 1 -C 4 )alkylcelluloses, in particular hydroxypropylmethylcelluloses (for example, Meth
• the cellulose-based polymers according to the present invention are cellulose-based polymers which preferably do not comprise a fatty chain, i.e. which preferably do not comprise a chain comprising more than 10 carbon atoms.
• the cellulose-based polymer(s) of the invention may be present in the dye composition of the invention in contents ranging from 0.05% to 10% by weight, in particular from 0.1% to 5% by weight and better still from 0.1% to 3% by weight, relative to the total weight of the composition.
• the composition comprises at least one amphoteric or zwitterionic surfactant.
• amphoteric or zwitterionic surfactant(s), which are preferably non-silicone, which may be used in the present invention may especially be derivatives of optionally quaternized aliphatic secondary or tertiary amines, in which derivatives the aliphatic group is a linear or branched chain comprising from 8 to 22 carbon atoms, said amine derivatives containing at least one anionic group, for instance a carboxylate, sulfonate, sulfate, phosphate or phosphonate group.
• cocoamphodiacetate sold by the company Rhodia under the trade name Miranol® C2M Concentrate.
• amphoteric or zwitterionic surfactants mentioned above, use is preferably made of the surfactants of formula (II) alone, or as mixtures.
• the content of amphoteric or zwitterionic surfactant(s) ranges from 0.05% to 30% by weight, preferably from 0.5% to 10% by weight and more preferably from 0.1% to 5% by weight, relative to the total weight of the composition.
• composition of the invention may also comprise at least one common cosmetic ingredient, chosen especially from propellants; oils; solid fatty substances and in particular C 8 -C 40 esters; C 8 -C 40 acids; C 8 -C 40 alcohols; surfactants other than those described previously; sunscreens; moisturizers; antidandruff agents; antioxidants; chelating agents; nacreous agents and opacifiers; plasticizers or coalescers; fillers; silicones and in particular polydimethylsiloxanes; polymeric or non-polymeric thickeners; gelling agents; emulsifiers; polymers, in particular conditioning or hairstyling polymers; fragrances; basifying agents or acidifying agents; silanes; crosslinking agents.
• the composition can, of course, comprise several cosmetic ingredients appearing in the above list.
• composition may in particular comprise one or more organic solvents, in particular water-soluble solvents, such as C 1 -C 7 alcohols; mention may in particular be made of C 1 -C 7 aliphatic monoalcohols, C 6 -C 7 aromatic monoalcohols, C 3 -C 7 polyols or C 3 -C 7 polyol ethers, which may be employed alone or as a mixture with water.
• organic solvents such as C 1 -C 7 alcohols
• water-soluble solvents such as C 1 -C 7 alcohols
• the normal cosmetic ingredients can be present in normal amounts which can be easily determined by those skilled in the art and which can be, for each ingredient, between 0.01% and 80% by weight. Those skilled in the art will take care to choose the ingredients included in the composition, and also the amounts thereof, such that they do not harm the properties of the compositions of the present invention.
• the pH of the composition is less than 4 and preferably ranges from 1 to 3, better still from 1.7 to 3.
• composition according to the invention is preferably in the form of styling or care gels, care lotions or creams, conditioners, masks or sera.
• composition according to the invention may be obtained by mixing several compositions.
• the process of the invention comprises the application of the composition described previously, followed by a step of straightening the hair with an iron.
• Straightening with an iron is known from the prior art. It consists in straightening the hair with flat heating tongs, which are generally metallic.
• the straightening irons are generally used at a temperature ranging from 150 to 250° C.
• the process of the invention may comprise other intermediate steps aimed at improving the straightening of the hair.
• the process of the invention comprises the application of the composition of the invention to dry hair, and a time of contact of the composition with the hair of between 10 and 60 minutes and preferably between 20 and 40 minutes. After this leave-on time, straightening with a brush and with a hairdryer (blow-drying) is performed. The hair is then straightened with a straightening iron at a temperature of between 150 and 250° C. and preferably from 210 to 230° C.
• the process of the invention may comprise the application of other hair agents as a pretreatment or post-treatment to the glyoxylic acid.
• it may comprise the application of a conditioning care product as a post-treatment.
• the hair straightening process comprises a step of washing the hair and then of drying with a hairdryer before applying the composition of the invention.
• the steps described above are then encountered, such as the contact time of the composition, the blow-drying, the straightening with a straightening iron, the application of a conditioning agent and the rinsing, all these steps possibly being performed independently of each other.
• the straightening with a straightening iron is performed in several passes on the hair, in general 8 to 10 passes.
• composition according to the invention (the contents are indicated as crude starting material (in grams of the commercial product indicated))
• Hydroxypropylmethylcellulose (Methocel F4M from Dow 1 Chemical) Glyoxylic acid (50% aqueous solution) 16 Disodium cocoamphodiacetate (sodium N-cocoylamidoethyl-N- 2 ethoxycarboxymethyl glycinate) 30% aqueous solution (Miranol C2M Conc. NP from Rhodia) Crosslinked ethyltrimethylammonium methacrylate chloride 2.5 homopolymer, as a dispersion in a mix.
• esters at 50%; (Salcare SC 96 from BASF) Lactic acid 2.5 Sodium hydroxide (10% aqueous solution) 7 Bisamino PEG/PPG-41-3 aminoethyl PG-propyl dimethicone at 2 30% AM (Silsoft A 843 from Momentive Performance Materials) Water qs *pH 2.2 ⁇ 0.2
• the above composition is applied to a lock of hair having a substantial level of curliness. After a leave-on time of 20 minutes on the hair, blow-drying is performed with a hairdryer and the lock is then straightened using a straightening iron. The evolution of fumes during the use of the iron is low.
• the lock is then washed, and then dried with a hairdryer. A straight lock of hair free of curliness is thus obtained.

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• 2012
  • 2012-11-09 FR FR1260658A patent/FR2997844B1/fr not_active Expired - Fee Related
• 2013
  • 2013-11-07 US US14/441,206 patent/US20150297488A1/en not_active Abandoned
  • 2013-11-07 WO PCT/FR2013/052668 patent/WO2014072644A1/fr not_active Ceased
  • 2013-11-07 BR BR112015009905-0A patent/BR112015009905B1/pt active IP Right Grant
  • 2013-11-07 EP EP13801637.3A patent/EP2916805B1/fr active Active
• 2017
  • 2017-06-13 US US15/621,461 patent/US20170273884A1/en not_active Abandoned

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